Production of camphene.



nnencnnar Bnnesj or LiIDWIGSHAFEN-ON-THE-RHINE, GERMANY,

nssrenon ro masonic alarms a SODA FABRIKQOF, unwres rnarnn-on-rnn-nnmn"GERMANY, A ooaroaarron.

I edoubt-ion or? CANIPl-lE-N.

No. 833,666. i I Specification of Letters Patent. Patented Oct. 16,1906.

' Application filed July 30,1906. Serial No- 328,450.

T l whOWb it m y 6011106171,," necessary to combine with all of thealkali Be it known that I, ENGELBERT Bnnes, used.

doctor of philosophy and chemist, asubject of Instead of the simplestphenol (C H OI-I) 5 the'King of Prussia, German Emperor, re otherphenols-such, for instance, as ortho- 5 siding atLudwigshafen-on-the-Rhine, Gercresol or alpha-naphthol or betanaphtholmany, have invented new and useful Imcan be employed, and I include allthese rovements in the Production of-Camphene, compounds under thegeneric term pheof which the following is a specification. nol. 60 Thepreparation of camphene by melting The following examples will serve to{ur- [o pinene hydrochlorid with alkali phenolate ther illustrate thenature of my invention has been described by Reychler in the Balleandthe method of carrying it into practical tin de la Socit Uhtmigae deParis, (3,) 15, effect; but my invention is not confined to 871, and inthe Berichtc vol. 29, 696. In the these examples. The parts are byweight. 65 method therein described, however, the al- Example 1: Mixtogether one thousand r kali phenolate used is freeor practically free(1,000) parts of solid pinene hydrochlorid, from Water, the authorstating that before nine hundred (900) parts of phenol, twointroducingthe pinene hydrochlorid the alhundred and thirty (230) parts of caustickali phenolate is;to be heated to a temperasoda, and six hundred (600)parts of water 70 ture of 175 centigrade in order to remove and heat themixture in an autoclave while the water. stirring for from five (5) tosix (6) hours at a I have now discovered that the manufactemperature ofone hundred and sixty (160) ture of camphene from pinene hydrochloriddegrees centigrade. When the mixture is can be carried out much moreeasily by heatcool, pour off the liquid from the sodium 75 ing thepinene hydrochlorid with an aqueous chlorid which has crystallized out,add exsolution of an alkali phenolate. cess of caustic soda to theliquid, and distil The present process possesses many advanoff thecamphene by means of steam. tages over the process described in theabove Example 2: Mix together one thousand references. In pa' ticularthe tedious opera- (1,000) parts of solid pinene hydrochlorid, 8o tionof preparing alkali phenolate iii the drymgone thousand (1,000) parts oforthocresol, form is dispensed with, it being only neeestwo hundred andforty (240) parts of caustic sary to dissolve the phenol in aqueouscaustic soda, and eight hundred (800) parts of waalkali solution andthen to introduce the ter and treat the mixture in the manner depinenehydrochlorid and to heat the mixture. scribed in the foregoing Example1.. 8 5 After the reaction has taken place excess of Example 32-Mixtogether one thousand 35 alkali is preferably added, and the camphene(1,000) parts of solid pinene hydrochlorid,

formed isdistilled off by means of steam, eleven hundred (1,100) partsof alpha-naphwhereupon the solution of alkali phenolate thol, twohundred and forty (240) parts of which, remains behind can, after theaddition caustic soda, and about eight hundred (800) of phenol to fixthe excess of alkali, and, if parts of water and treat the mixture inthe 4o necessary, after evaporating down to the remanner described inthe foregoing Example quired concentration, be employed directly 1. Inthis example beta-naphthol can be to react upon a fresh quantity ofpinene hyused instead of alpha-naphthol.

drochlorid. This constitutes a further ad- In all of the above examplesthe uantity 5 vantage over Reychlers process, for when of water employedcan be varied wit in con- 4 5 pine'ne hydrochlor'd is melted with dryalkali siderably large ranges.

phenolate a more or less darkly-colored re- I claimaction product isobtained, a part of the phe- 1. The process of producing camphene by nolbeing destroyed and the remainder of the heating pinene hydrochloridwith an aqueous 10o phenol has to be purified before it canconvensolution of an alkali salt of a phenol whereby 5o iently be usedover again. the use of steam distillation is rendered pos- I prefer tocarry out the reaction in the 'sible and the decomposition of theresidue is presence of an excess of phenol over that obviated.

2. The process of producing 'eamphene by whereby the use of steamdistillation is renheating pinene h droahlorid with an aqueous deredpossible and the decomposition of the solution of so ium phenolate (O HONa) I residue is obviated.

whereby the use of steam distillation is renn testimony whereof Ihavehereunto set 5 dered possible and the decomposition of the my handin the presence of two subscribing 15 residue is obviateda v Witnesses.v- The process of producing eamphene by EN GELBERT BERGS. heating pinenehydrochlorid with an aqueous Witnesses: solution of sodium'phenolate (CH ONa) in I J. ALEO. LLOYD,

10 the presence of an excess of phenol (C H Ofl) H-. W. HARRIs

